(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

Base Information

Chemical Name:(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole
CAS No.:1415010-39-7
Molecular Formula:C₂₉H₄₆N₂O₅SSi
Molecular Weight:562.846
Hs Code.:

Synonyms:(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

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Chemical Property of (3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

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Technology Process of (3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

There total 18 articles about (3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

: 1415010-38-6
2-(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3-[(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indol-3a-yl]acetaldehyde

: 24470-78-8
isopropyltriphenylphosphonium iodide

: 1415010-39-7
(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

Guidance literature:: isopropyltriphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

2-(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3-[(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indol-3a-yl]acetaldehyde; In tetrahydrofuran; at 0 - 20 ℃; for 10h; Inert atmosphere;
DOI:10.1021/ol302880x

Reference yield:

: 1415010-31-9
(3aS,5aS,9aS,9bR)-3a-allyl-6,6,9a-trimethyl-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

: 1415010-39-7
(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

Guidance literature:: Multi-step reaction with 3 steps

1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetonitrile / 17 h / 20 °C / Inert atmosphere

2.1: sodium periodate / tetrahydrofuran; water / 2 h / 20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 10 h / 0 - 20 °C / Inert atmosphere

With sodium periodate; osmium(VIII) oxide; n-butyllithium; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; water; acetonitrile;
DOI:10.1021/ol302880x

Reference yield:

: 60134-39-6
(-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one

: 1415010-39-7
(3aS,5aS,9aS,9bR)-6,6,9a-trimethyl-3a-(3-methylbut-2-enyl)-3-(2-nitrobenzenesulfonyl)-9b-(trimethylsilyloxy)perhydro-1H-benzo[e]indole

Guidance literature:: Multi-step reaction with 18 steps

1.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid; water / dichloromethane / 0.33 h / 0 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

4.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C

5.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

5.2: 0.08 h / Inert atmosphere

6.1: tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C

8.1: cyclohexane; borane-THF / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

8.2: 0.5 h / 20 °C / Inert atmosphere

9.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 - 20 °C / Inert atmosphere

10.1: hydrazine / chloroform / 0.33 h / 20 °C

11.1: acetic acid / ethanol / 12 h / Reflux

12.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

12.2: 0.08 h / 0 °C

13.1: tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

14.1: pyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

14.2: 24 h / 20 °C / Inert atmosphere

15.1: triphenylphosphine; acetic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine / tetrahydrofuran / 20.17 h / 20 °C / Inert atmosphere

16.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetonitrile / 17 h / 20 °C / Inert atmosphere

17.1: sodium periodate / tetrahydrofuran; water / 2 h / 20 °C

18.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

18.2: 10 h / 0 - 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium periodate; osmium(VIII) oxide; n-butyllithium; borane-THF; cyclohexane; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; water; toluene; acetonitrile;
DOI:10.1021/ol302880x